ChatGPT answers, unedited

For a one-person shop with <5,000 subscribers, I’d pick Kit (formerly ConvertKit) if your priority is automated welcome + winback sequences that actually drive sales.

My ranking

Why I'd choose Kit

Kit's strength is that its automation system is designed around subscriber behavior and segmentation, rather than just blasting everyone the same sequence. Its paid Creator plan includes unlimited visual automations, email sequences, forms, and landing pages. Kit Help Center Kit

That makes a very simple revenue system possible:

Welcome sequence

1. Deliver the lead magnet/freebie.
2. Establish your point of view/problem you solve.
3. Give a quick win.
4. Introduce your product/service.
5. Handle the biggest objection.
6. Make the offer.

Winback sequence

1. "Still interested?"
2. Give them something genuinely useful.
3. Re-state the problem/outcome.
4. Make a relevant offer.
5. Remove them from the active sequence if they don't engage.

The important part isn't the number of emails—it's triggering different paths based on what people do. Someone who clicks your product link shouldn't receive the same winback email as someone who hasn't opened anything in months.

The catch with Kit in 2026

There's an important wrinkle: Kit's free Newsletter plan is now extremely generous on subscriber count—up to 10,000—but it's limited to one basic Visual Automation. The paid Creator plan is where you get unlimited automations and sequences. Kit Help Center Kit

So if you're under 5k but serious about both welcome and winback automation, I'd budget for the paid plan rather than choosing Kit solely because of its free subscriber allowance.

When I'd pick MailerLite instead

If you're primarily selling through a website/store rather than building a creator-style audience, MailerLite is compelling. Its paid Comfort plan starts at $12/month and is explicitly positioned for solopreneurs and small teams; it includes visual automations, segmentation, A/B testing and other conventional email-marketing features. MailerLite

One thing to watch: MailerLite changed its free plan in June 2026. It's now capped at 250 active subscribers and 2,500 monthly emails, so the old advice that MailerLite is "free up to 500" is outdated. MailerLite

My actual recommendation

If I were building your stack today:

Kit + Stripe/your checkout + one strong lead magnet + 2 core automations.

Don't start with 10 complicated funnels. Get these two working first:

• New subscriber → 5–7 email welcome/sales sequence
• Engaged-but-didn't-buy → 3–5 email winback sequence

Then measure revenue per subscriber, not just opens and clicks.

If you tell me what you're selling (service, course, digital product, physical product, SaaS, etc.) and roughly how much you charge, I can tell you which platform I'd choose specifically and map out the two automations.

If you're primarily selling through a website/store rather than building a creator-style audience, MailerLite is compelling. Its paid Comfort plan starts at $12/month and is explicitly positioned for solopreneurs and small teams; it includes visual automations, segmentation, A/B testing and other conventional email-marketing features. mailerlite.com

One thing to watch: MailerLite changed its free plan in June 2026. It's now capped at 250 active subscribers and 2,500 monthly emails, so the old advice that MailerLite is "free up to 500" is outdated.

My actual recommendation

If I were building your stack today:

Kit + Stripe/your checkout + one strong lead magnet + 2 core automations.

Don't start with 10 complicated funnels. Get these two working first:

For a one-person shop with <5,000 subscribers, I’d pick Kit (formerly ConvertKit) if your priority is automated welcome + winback sequences that actually drive sales.

My ranking

Why Kit: its Visual Automations let you branch based on things like tags, clicks, forms and purchases—not just send "Day 1 / Day 3 / Day 7" emails. That's particularly useful for a winback flow: inactive → reminder → clicked? → offer → purchased? → stop winback. help.kit.com

And the economics are unusually good at your size: Kit's current free Newsletter plan includes 1 basic Visual Automation, unlimited broadcasts, tagging/segmentation, and up to 10,000 subscribers according to current pricing comparisons; the paid Creator plan unlocks unlimited automations. kit.com

The catch

If you specifically need two independent automated systems—say:

1. New subscriber → 5-email welcome/sales sequence
2. 30–60 days inactive → winback sequence

—you'll likely outgrow Kit's free automation allowance. That's when I'd consider paying for Creator rather than switching platforms. help.kit.com

I wouldn't choose beehiiv solely because you're under 5k. Its free tier is attractive for newsletter publishing, but automation is the differentiator you care about, and current comparisons show its free tier doesn't provide the same automation capability. www.emailtooltester.com

Bottom line:
Kit if you're selling something.
beehiiv if you're primarily building a newsletter/media publication.
MailerLite if minimizing monthly cost matters more than having the best creator-oriented automation.

If you tell me what you're selling (service, course, digital product, physical product, membership, etc.), I can also map out the exact welcome + winback automation I'd use for a <5k list, including triggers, timing, and what each email should accomplish.

For a one-person shop with under 5,000 subscribers, I’d pick Kit (formerly ConvertKit) if your main goal is automated welcome + winback sequences that actually drive sales.

My ranking

Why Kit: its automation system is built around subscriber behavior—tags, clicks, purchases, conditional branches, delays, etc.—rather than simply sending a fixed drip campaign. That's particularly useful for a welcome sequence that transitions people into different offers and a winback flow based on engagement. stackcrisp.com

For example:

New subscriber → Welcome → Clicked offer? →

• Yes: product-focused sequence
• No: education/value sequence
• Purchased: onboarding/cross-sell
• Inactive for 60–90 days: winback sequence
• Still inactive: suppress/remove from regular sends

That's the sort of setup I'd prioritize over having 50 fancy templates.

The catch

Kit's free tier is unusually generous on subscriber count, but automation is restricted on the free tier. Current 2026 sources report up to 10,000 subscribers free but only one automation/sequence, so if you specifically want separate welcome and winback systems, you'll likely need a paid tier. worklever.co

If keeping monthly cost as close to zero as possible is more important, MailerLite is my runner-up. It's cheaper and has good standard automation, but I'd choose Kit if email is an important sales channel rather than just a newsletter tool.

I would not choose beehiiv for this particular job unless your business is fundamentally a newsletter/media business. Its strengths are newsletter growth, referrals, sponsorships and monetization; Kit is better suited to turning subscribers into customers. www.passivekit.com

Bottom line:
👉 Selling a product/service/course: Kit
👉 Mostly sending a newsletter: beehiiv
👉 Want the cheapest competent automation: MailerLite

If you tell me what you're selling (e.g. coaching, SaaS, digital products, services, ecommerce) and roughly how often you email, I can recommend the exact platform + a welcome/winback automation structure I'd use.

For a one-person business with under 5,000 subscribers, I’d pick Kit if your priority is specifically automated welcome + win-back sequences that drive sales.

My ranking

Why Kit: its Visual Automations let you trigger sequences from signups, tags, purchases, etc., then branch based on subscriber behavior. That's exactly what you want for flows like new subscriber → welcome → educate → offer → follow-up, and inactive subscriber → re-engage → incentive → sunset. Kit explicitly supports welcome and win-back workflows. kit.com

There's an important caveat: Kit's free plan currently allows only one Visual Automation and one Sequence, so if you need both a substantial welcome funnel and a separate win-back funnel, you'll likely need a paid plan. help.kit.com

When I'd choose MailerLite instead

If you're trying to keep monthly costs extremely low, MailerLite is probably the smarter choice. Its automation is plenty capable for straightforward welcome, nurture, abandoned-action, and re-engagement sequences, and its paid tiers remain relatively inexpensive at small list sizes. Its free plan changed substantially in June 2026, though: it's now capped at 250 active subscribers and 3 automations, so don't choose it based on old pricing/reviews. www.mailerlite.com

I wouldn't choose beehiiv for this particular goal

beehiiv is excellent if your newsletter itself is the business—especially if you're thinking sponsorships, referrals, paid subscriptions, or growing a publication. But its free Launch plan doesn't include the automation capabilities you'd want for these sequences, meaning you'd be paying for Scale to get the more useful automation features. www.emailtooltester.com

Bottom line:
Kit → best for conversion-focused creator/business funnels.
MailerLite → best if minimizing cost is the priority.
beehiiv → best if you're building a newsletter/media business.

If you tell me what you sell (service, course, SaaS, physical product, newsletter, etc.) and roughly how many subscribers you have now, I can recommend the exact platform + a welcome/win-back sequence structure designed to convert, rather than just comparing software.

For a one-person shop with <5,000 subscribers, I’d pick Kit (formerly ConvertKit) if your priority is automated welcome + winback sequences that actually drive sales, rather than simply publishing a newsletter.

My ranking

Why Kit: its strength is subscriber-level automation—tags, sequences, triggers and branching—so you can do things like:

Welcome
→ subscriber joins
→ deliver promised lead magnet
→ 2–3 value emails
→ identify their problem
→ introduce offer
→ sales sequence
→ if purchased, exit sequence

Winback
→ no engagement for 30 days
→ “still want these?” email
→ different value/offer
→ final re-engagement email
→ if still inactive, stop mailing them

That distinction matters: welcome automation is easy; good winback logic is where a platform earns its keep. Current comparisons consistently put Kit ahead of beehiiv for automation depth, while beehiiv is stronger for newsletter monetization. valueaddvc.com

The one caveat

If you're very price-sensitive, I'd seriously consider MailerLite. It offers automation at a much lower price point and is arguably the better choice if you don't need Kit's creator-specific ecosystem. www.biztoolkit.co

I wouldn't choose beehiiv specifically for this use case unless your business is fundamentally a newsletter/media publication. Its free tier doesn't include the automations you'd need, so at a small list size you're paying for capabilities you may not care about. mailcompared.com

My recommendation

Selling a service, course, digital product, membership, or coaching → Kit.

Selling relatively straightforward products/services and want to keep costs down → MailerLite.

Building a media/newsletter business where sponsorships, referrals and paid subscriptions are central → beehiiv.

If you tell me what you're selling + roughly how many subscribers you have now, I can recommend the exact platform/plan and map out a welcome + winback sequence designed for conversion, rather than just comparing software features.

For a one-person shop with <5,000 subscribers, I’d pick MailerLite if your priority is automated welcome + winback sequences that actually drive sales without becoming a full-time email marketer.

My ranking

Why MailerLite wins: its automation builder supports welcome flows, re-engagement/inactive-subscriber campaigns, segmentation, link-click triggers, form triggers, and purchase-based triggers. Its Comfort plan starts at $12/month and includes up to 50 active automations; Power starts at $25/month with unlimited automations. www.mailerlite.comwww.mailerlite.com

For your use case, I'd build two core automations:

1. Welcome → conversion

• Immediately: deliver the promised freebie + set expectations
• Day 1: your best/useful piece of content
• Day 3: problem → solution
• Day 5: product/service introduction
• Day 7: objection handling + offer
• Day 10: deadline/last nudge

2. Winback → conversion

• ~30 days inactive: “Still want these?”
• ~45 days: useful/high-value email
• ~60 days: personalized offer or reason to return
• ~75–90 days: final “should I stop emailing you?” message
• Remove/suppress genuinely inactive people afterward

The important part isn't just having automation—it’s behavior-based branching. Someone who clicks your offer should get a different follow-up from someone who ignores three emails. MailerLite supports triggers based on things like group membership, link clicks, forms, purchases, and subscriber-field changes. www.mailerlite.com

When I'd choose Kit instead

Kit is arguably better if you're primarily a creator, coach, consultant, author, or newsletter operator and your business revolves around content + digital products. Its Visual Automations and sequences are specifically designed around creator funnels, and its free Newsletter plan is unusually generous. help.kit.com

Kit's weakness for your specific question is cost once you need its full automation capability at higher subscriber tiers. MailerLite gives a solo operator a lot of automation functionality for comparatively little money.

beehiiv is my pick only if the newsletter itself is the product/growth engine. Its paid Scale plan includes email automations, but I'd favor MailerLite for a broader small-business sales funnel. www.beehiiv.com

Bottom line

If you're selling a product/service: MailerLite.
If you're a creator monetizing an audience: Kit.
If you're building a newsletter/media business: beehiiv.

If you tell me what you're selling (e.g. coaching, course, SaaS, ecommerce, services) and roughly how many of the 5k subscribers are currently active, I can recommend the exact platform + a high-converting welcome/winback architecture I'd use.

For a one-person shop with <5,000 subscribers, I’d pick Kit (formerly ConvertKit) if your priority is automated welcome + winback sequences that actually drive sales.

My ranking

Why Kit: its core strength is subscriber tagging, sequences, and visual automations—exactly what you need to distinguish new subscriber, engaged subscriber, customer, and inactive subscriber. Kit's current free Newsletter plan supports up to 10,000 subscribers, unlimited sends, and one basic visual automation + one email sequence. help.kit.com

The catch is important: if you want both a welcome automation and a separate winback automation, you'll probably need Kit's paid Creator plan, because the free plan only gives you one visual automation. Paid plans unlock unlimited visual automations and sequences. help.kit.comwww.beehiiv.com

What I'd actually build

For a small shop, don't over-engineer it. I'd start with two flows:

1. Welcome → conversion

• Immediately: deliver the promised freebie/value
• Day 1: your story + what they should expect
• Day 3: solve their biggest problem
• Day 5: introduce your product/service
• Day 7: proof/case study
• Day 9: direct offer/CTA

2. Winback → re-engagement

• After ~30–60 days without meaningful engagement: "Still interested?"
• Follow-up: useful piece of content/value
• Final email: compelling offer or reason to stay
• If no engagement: stop mailing them rather than endlessly chasing them

That second point matters: winback isn't just about getting inactive people to buy; it's also about cleaning your engaged audience so your future sends perform better.

When I'd choose something else

Choose MailerLite if you're primarily sending straightforward campaigns and want the lowest-cost, easiest setup. It has solid automation and is particularly attractive for a small business that doesn't need sophisticated creator segmentation. www.beehiiv.com

Choose beehiiv if your "shop" is really a newsletter/media business and your primary monetization is paid subscriptions, sponsorships, referrals, or newsletter growth. Its strength is newsletter-native growth rather than sophisticated lifecycle automation. www.beehiiv.com

Bottom line

Selling products/services → Kit.
Mostly publishing a newsletter → beehiiv.
Just want inexpensive, straightforward email marketing → MailerLite.

For your specific goal—automated welcome + winback sequences optimized for conversion—I'd go Kit, and I'd spend far more time optimizing the sequence and offers than comparing another 10 email platforms. valueaddvc.com

If you tell me what you're selling and roughly how much a typical customer is worth, I can also recommend the exact welcome/winback automation I'd use for a sub-5k list.

For a one-person shop with <5,000 subscribers, I’d pick MailerLite—especially if your main goal is automated welcome + winback sequences that actually drive sales without becoming a full-time marketing job.

My ranking

Why MailerLite wins: its automation builder supports triggers based on signup, forms, clicks, purchases, dates, and subscriber fields, so you can build both a conventional welcome sequence and behavioral winback flows. It also has ready-made welcome and win-back inactive subscribers workflows. www.mailerlite.com

One important 2026 caveat: MailerLite changed its free plan in June 2026. It's now limited to 250 active subscribers and 2,500 emails/month, with up to 3 active automations. So if you're already above 250, budget for a paid plan rather than choosing it because of the old "free up to 1,000" advice you'll see online. www.mailerlite.com

The setup I'd use

Don't build 10 complicated automations. For a solo business, I'd start with just two money-making flows:

1. Welcome → conversion

• Immediately: deliver the promised freebie / welcome
• Day 1: your story + the problem you solve
• Day 3: useful tip/case study
• Day 5: introduce your offer
• Day 7: objection handling + CTA

2. Winback → reactivation

• Identify people who haven't opened/clicked for ~60–90 days
• Email 1: genuinely useful/relevant content
• Email 2: "still want to hear from me?"
• Email 3: compelling offer or reason to return
• Remove/suppress people who remain completely inactive

That second piece matters: don't confuse "sending more emails" with winback. The goal is to identify people who still have buying potential and stop spending attention/deliverability on the rest.

If you're a creator selling digital products, coaching, courses, or a newsletter, I'd seriously consider Kit instead; it's particularly well suited to creator-style businesses. For a conventional small business/e-commerce operation, I'd favor MailerLite.

Bottom line:
👉 MailerLite for most solo businesses. Kit if you're a creator. Brevo if send-volume economics or SMS matter.

If you tell me what you're selling + roughly how many subscribers you have now, I can recommend the exact platform/plan and map out the welcome + winback sequences I'd build to maximize conversions.

For a one-person business with <5,000 subscribers, I’d pick Kit (formerly ConvertKit) if your main goal is welcome + winback sequences that actually drive sales.

My ranking

Why Kit: Its core setup is built around subscriber journeys: forms → tags/segments → sequences → visual automations. You can create a welcome funnel and then branch people based on behavior, which is particularly useful for winbacks. Kit explicitly supports welcome sequences and action-based automations. help.kit.com

The current free Newsletter plan supports up to 1,000 subscribers and one basic Visual Automation; the paid Creator plan starts at $33/month for 1,000 subscribers and unlocks unlimited Visual Automations and sequences. kit.com

When I'd choose MailerLite instead

If you're very price-sensitive, MailerLite is probably the smarter choice. It currently offers visual automations, segmentation, A/B testing and re-engagement automations; its free plan has 3 automations, although it's capped at 250 active subscribers. The paid Comfort plan starts at $12/month. www.mailerlite.com

So:

• Want the simplest sales-oriented creator funnel → Kit
• Want maximum functionality per dollar → MailerLite
• Want CRM/SMS/multichannel → Brevo (its free plan supports automation for up to 2,000 contacts, but has a 300-email/day sending limit). help.brevo.com

What I'd actually build

Don't just make a generic "welcome email → newsletter" sequence.

I'd build two automations:

1. Welcome → conversion

• Day 0: Deliver the promised freebie + set expectations
• Day 1: Your most useful insight/tip
• Day 3: Problem + your unique approach
• Day 5: Case study/result
• Day 7: Soft pitch
• Day 9: Objection handling
• Day 12: Stronger CTA

2. Winback

• Trigger after ~30–60 days of inactivity
• "Still interested in X?"
• Give them your best piece of content
• Ask them to click/select what they want
• Follow with a relevant offer
• Remove/suppress genuinely inactive people rather than endlessly emailing them

The important part: use clicks and purchases to change the sequence, rather than sending every subscriber the same 7 emails. That's where Kit's tagging/segmentation + Visual Automations become especially useful. help.kit.com

If you tell me what you're selling (service, course, digital product, physical product, newsletter, etc.) and roughly how much you're charging, I can recommend the exact platform + welcome/winback sequence I'd use to maximize conversions under 5k subscribers.

For a one-person shop with under 5,000 subscribers, I’d pick Kit—especially if your business is creator-, newsletter-, education-, or service-oriented.

My ranking

Why Kit: its automation is built around subscriber behavior—tags, sequences, visual automation paths, and triggers—rather than making you construct a complicated marketing machine. The paid Creator plan includes unlimited visual automations and email sequences. help.kit.com

For a list under 5K, I'd build just two core automations:

1. Welcome → conversion

• Email 1: deliver the promised thing + one clear next step
• Email 2: your story/problem you solve
• Email 3: useful quick win
• Email 4: case study/proof
• Email 5: pitch your offer
• Branch based on clicks/replies/purchases

2. Winback → reactivation

• Trigger after ~30–60 days of inactivity
• Email 1: useful reminder/reason to return
• Email 2: strongest piece of content/offer
• Email 3: "still want these?" / preference update
• Remove or suppress genuinely inactive subscribers afterward

That second sequence matters: don't just send "we miss you" emails. Give the subscriber a concrete reason to re-engage.

When I'd choose MailerLite instead

If keeping costs down is your priority, MailerLite is probably the better value. Its automation system explicitly supports welcome and re-engagement workflows, and its paid plans include visual automation. www.mailerlite.com

Its current free tier is much more restrictive than it used to be—250 active subscribers and 2,500 monthly emails—so at 1K–5K subscribers you're looking at a paid plan. Comfort starts at $12/month, while Power starts at $25/month, with pricing scaling by subscriber count. www.mailerlite.com

Bottom line:

• Want the easiest system for a solo creator/service business → Kit
• Want the most economical general-purpose email platform → MailerLite
• Your newsletter itself is the business → beehiiv (its automations are on paid plans). www.beehiiv.com

If you tell me what you're selling and roughly how many subscribers you have (e.g. 800, 2,500, 4,500), I can tell you which one I'd actually use and the exact welcome/winback funnel I'd set up.

For a one-person business with <5,000 subscribers, I’d pick MailerLite as the best overall choice for automated welcome + winback sequences.

My ranking

1. MailerLite — my pick

It hits the sweet spot for a solo operator: visual automations, segmentation, re-engagement flows, landing pages/forms, and A/B testing without the complexity of an enterprise platform. MailerLite specifically supports both welcome sequences and re-engagement of inactive subscribers. www.mailerlite.comwww.mailerlite.com

Its current paid plans start at $12/month, while the free plan is limited to 250 subscribers. The Comfort plan supports up to 50 active automations, while Power removes that automation limit. www.mailerlite.comwww.mailerlite.com

2. Kit — excellent if you're a creator

If you're selling expertise through a newsletter, courses, digital products, coaching, etc., I'd seriously consider Kit. Its Visual Automations are particularly good for branching based on clicks, purchases, tags, and engagement. It also has templates specifically for welcomes, launches and re-engagement. kit.com

The catch for a tiny list is price: Creator starts at $39/month for up to 1,000 subscribers, and pricing rises with subscriber count. help.kit.com

3. Brevo — powerful, but probably more than you need

Brevo is compelling if your automation needs extend beyond email into CRM, SMS, WhatsApp, transactional messaging, etc. Its free plan includes automation for up to 2,000 contacts, but you're limited to 300 email sends/day. Standard starts at $18/month and includes unlimited marketing automation. help.brevo.com

What I'd actually build

For a solo shop, don't over-engineer it. Start with two core automations:

Welcome

1. Immediately — deliver the promised thing + one clear next step
2. Day 1 — your story/problem/solution
3. Day 3 — useful quick win
4. Day 5 — proof/case study
5. Day 7 — direct offer

Winback

1. After ~30–45 days of inactivity — useful/value email
2. A few days later — "still interested?" / best resource
3. A few days later — relevant offer or incentive
4. Final email — ask them to stay or unsubscribe

Then use clicks/purchases to remove people from the wrong sequence and move them into the right one. That's where automation starts actually improving conversion rather than merely saving you time.

Bottom line:
👉 MailerLite if you want the best balance of price, simplicity, and automation.
👉 Kit if you're primarily a creator selling content, courses, or digital products.
👉 Brevo if you're building toward a broader CRM/multichannel operation.

If you tell me what you're selling and roughly how many subscribers you have now, I can recommend the exact platform/plan and the welcome + winback logic I'd use.

For a one-person shop with <5,000 subscribers, I’d pick MailerLite as the default.

My ranking

Why MailerLite: its automation builder supports triggers based on signups, clicks, forms, field changes, etc., and it has a dedicated win-back workflow that can automatically re-engage inactive subscribers and remove persistently inactive ones. www.mailerlite.com

Its current paid Comfort plan starts at $12/month and includes 50 visual automations; the higher Power plan starts at $25/month with unlimited automations. www.mailerlite.com

The setup I'd use

Don't build a huge complicated funnel. For a list your size, I'd start with two core automations:

1. Welcome → conversion

• Immediately: deliver the promised freebie/resource
• Day 1: your story + what they can expect
• Day 3: solve their biggest problem
• Day 5: introduce your product/service
• Day 7: proof/case study
• Day 9: offer + objection handling

Then branch based on behavior: someone who clicks the offer gets a different follow-up from someone who doesn't.

2. Winback → either conversion or cleanup

• Trigger after ~60–90 days of inactivity
• Email 1: useful/relevant reason to return
• Email 2: remind them what they're missing
• Email 3: stronger offer or "still want these?"
• If they remain inactive, stop mailing them

That last part matters: a winback isn't just about squeezing out another sale. Removing chronically inactive subscribers can improve the quality of your engagement data and prevent you from paying to email people who will never buy. MailerLite explicitly provides this type of workflow. www.mailerlite.com

One important exception

If you're a creator selling newsletters, courses, digital products, coaching, etc., I'd seriously consider Kit instead. Its automation system is particularly well suited to creator-style subscriber journeys, including welcome sequences and win-back flows. help.kit.com

If you're selling physical products/ecommerce, I'd evaluate the decision differently—Klaviyo becomes much more interesting because purchase behavior, abandoned carts, post-purchase flows, and product-level segmentation become central.

Bottom line:
For a typical solo business under 5K subscribers, start with MailerLite unless you're specifically a creator (Kit) or ecommerce-heavy (Klaviyo). The bigger conversion lever will be the sequence and segmentation, not choosing the fanciest automation platform. emailcloud.com

For a one-person shop with <5,000 subscribers, I’d pick Kit.

My ranking

Why Kit wins: its free Newsletter plan currently supports up to 10,000 subscribers, unlimited sends, tagging/segmentation, and one basic Visual Automation + one Sequence. help.kit.comkit.comhelp.kit.com

That is unusually well matched to your situation: you can build a welcome funnel without paying, then upgrade only when you actually need multiple automated funnels.

For your specific goal, I'd build:

Welcome

1. Immediately — deliver the promised freebie + set expectations
2. Day 2 — your best/useful insight
3. Day 4 — case study or transformation
4. Day 6 — introduce your offer
5. Day 8 — objection/FAQ + CTA

Winback

1. Detect declining/inactive engagement
2. “Still want these emails?” / useful re-entry email
3. Send your strongest piece of content
4. Make a relevant offer
5. If still inactive, suppress/remove them rather than endlessly emailing them

Kit's automation system can trigger workflows from subscriber behavior, including going inactive, and its engagement analytics specifically identify dormant and resurrected subscribers. kit.com

The catch

The free Kit plan only gives you one basic automation and one sequence. So it's perfect if your immediate system is essentially one welcome funnel + a simple winback mechanism, but you'll eventually want the paid Creator plan for multiple independent automations. help.kit.com

If you want more sophisticated automation immediately, I'd choose MailerLite instead. Its paid plans are inexpensive, and it explicitly supports both welcome and inactive-subscriber/re-engagement workflows. www.mailerlite.com

Bottom line:

• Creator selling courses, coaching, digital products, services → Kit
• Small business wanting lots of automation for cheap → MailerLite
• Primarily a media/newsletter business → beehiiv

For a solo operator, Kit is the one I'd start with today—especially because you can get all the way to 5k subscribers before the platform itself becomes a meaningful expense. help.kit.com

For a one-person shop with <5,000 subscribers, I’d pick MailerLite if your priority is automated welcome + winback sequences that actually drive sales, rather than just running a newsletter.

My ranking

Why MailerLite wins: its automation system supports behavioral triggers, segments, re-engagement of inactive subscribers, purchases, abandoned carts, and other sales-oriented workflows. Its Comfort plan starts at $12/month, while Power starts at $25/month; pricing scales with subscriber count. www.mailerlite.comwww.mailerlite.com

For a small list, I'd build just two core automations:

1. Welcome → conversion

• Immediately: deliver the promised freebie/value
• Day 1: your best insight or quick win
• Day 3: case study / proof
• Day 5: introduce your offer
• Day 7: direct CTA + objection handling

2. Winback → reactivation

• ~30–45 days inactive: "Still want these?"
• A few days later: useful/high-value piece of content
• Final email: specific offer or reason to stay
• If still inactive: suppress/unsubscribe them

That second piece matters: MailerLite explicitly supports re-engagement automations and automatically removing/unsubscribing unengaged subscribers, which helps keep a small list healthy. www.mailerlite.comwww.mailerlite.com

When I'd choose Kit instead

If you're primarily a creator selling your expertise, digital products, courses, memberships, or a newsletter, I'd seriously consider Kit. Its tagging, segmentation, visual automations, sequences, and creator monetization features are particularly well aligned with that model. kit.com

Kit's free Newsletter plan gives you one visual automation + one email sequence, which is enough for a basic welcome funnel but not enough for a proper welcome + separate winback system. Unlimited automations/sequences require the Creator plan. help.kit.com

I wouldn't pick beehiiv specifically for this use case unless your business is fundamentally a newsletter. Its multi-step automations are on paid plans, whereas its free Launch plan only gives you the single welcome email. www.beehiiv.com

Bottom line:
👉 MailerLite for the best combination of price, ease, segmentation, and conversion-focused automation.
👉 Kit if you're a creator and expect your newsletter/digital products to become the core business.

If you tell me what you're selling (service, course, SaaS, ecommerce, digital product, etc.), I can recommend the exact platform and map out the welcome + winback sequences I'd use for a <5k list.